Synthesis of partially modified retro and retroinverso ψ[NHCH(CF3)]-peptides

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1827-1830

  Volonterio, Alessandro ^a   Bravo, Pierfrancesco ^b   Zanda, Matteo ^a  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE;

ARTICLE; BIOCHEMISTRY; CHEMISTRY; METHODOLOGY; MOLECULAR MIMICRY; SYNTHESIS;

BIOCHEMISTRY; MOLECULAR MIMICRY; PEPTIDES;

EID: 0034729603     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005876p     Document Type: Article

References (48)

1. (a) Olson G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039-3049.
2. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
3. (c) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305-341.
4. Fletcher, M. D.; Campbell, M. M. Chem. Rev. 1998, 98, 763-795.
5. (a) Goodman, M.; Chorev, M. Acc. Chem. Res. 1979, 12, 1-7.
6. (b) Chorev, M.; Willson, C. G.; Goodman, M. J. Am. Chem. Soc. 1977, 99, 8075-8076.
7. A conceptually related peptide bond surrogate ψ[CH(CN)NH] has been reported: (a) Herrero, S.; Suárez-Gea, M. L.; González-Muñiz, R.; García-López, M. T.; Herranz, R.; Ballaz, S.; Barber, A.; Fortuño, A.; Del Río, J. Bioorg. Med. Chem. Lett. 1997, 7, 855-860. For some recent examples of fluorine-containing peptidomimetics:
8. (b) Garrett, G. S.; McPhail, S. J.; Tornheim, K.; Correa, P. E.; McIver, J. M. Bioorg. Med. Chem. Lett. 1999, 9, 301-306.
9. (c) Poupart, M.-A.; Fazal, G.; Goulet, S.; Mar, L.-T. J. Org. Chem. 1999, 64, 1356-1361.
10. (d) Eda, M.; Ashimori, A.; Akahoshi, F.; Yoshimura, T.; Inoue, Y.; Fukaya, C.; Nakajima, M.; Fukuyama, H.; Imada, T.; Nakamura, N. Bioorg. Med. Chem. Lett. 1998, 8, 919-924 and references therein.
11. (e) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 4195-4198.
12. (f) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107-3111.
13. (g) Boros, L. G.; Decorte, B.; Gimi, R. H.; Welch, J. T.; Wu, Y.; Handschumacher, R. E. Tetrahedron Lett. 1994, 35, 6033-6036.
14. (h) Revesz, L.; Briswalter, C.; Heng, R.; Leutwiler, A.; Mueller, R.; Wuethrich, H.-J. Tetrahedron Lett. 1994, 35, 9693-9696.
15. (i) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309-7314.
16. See for example: Scolnick, L. R.; Clements, A. M.; Liao, J.; Crenshaw, L.; Hellberg, M.; May, J.; Dean, T. R.; Christianson, D. W. J. Am. Chem. Soc. 1997, 119, 850-851.
17. (a) Shibuya, A.; Kurishita, M.; Ago, C.; Taguchi, T. Tetrahedron 1996 52, 271-278. See also:
18. (b) Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Fluorine Chem. 1999, 97, 91-96.
19. This reaction is extraordinarily simple and efficient, if one considers that examples of 1,4-additions by chiral α-amino esters to 4-substituted Michael-acceptors are very scarce in the literature: (a) Urbach, H.; Henning, R. Tetrahedron Lett. 1984, 25, 1143-1146.
20. (b) Eckert, H. G.; Badian, M. J.; Gantz, D.; Kellner, H.-M-; Volz, M. Arzneim. Forsch. 1984, 34, 1435-1447. For Michael-type reactions of amines with 4-substituted acceptors:
21. (c) Burke, A. J.; Davies, S. G.; Hedgecock, C. J. R. Synlett 1996, 621-622.
22. (d) d'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112-8114.
23. (e) Cardillo, G.; Di Martino, E.; Gentilucci, L.; Tomasini, C.; Tomasoni, L. Tetrahedron: Asymmetry 1995, 6, 1957-1963.
24. (f) Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trerè, A. J. Org. Chem. 1993, 58, 5615-5619.
25. (g) Baldwin, S. W.; Aubé, J. Tetrahedron Lett. 1987, 28, 179-182.
26. (h) Hirama, M.; Shigemoto, T.; Yamazaki, Y.; Ito, S. J. Am. Chem. Soc. 1985, 107, 1797-1798.
27. (i) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Walters, I. A. S. Tetrahedron: Asymmetry 1994, 5, 35-36.
28. (j) Davies, S. G.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129-1139.
29. (k) Davies, S. G.; Ichihara, O.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1141-1147.
30. (l) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1994, 59, 649-652.
31. (m) Asao, N.; Shimada, T.; Sudo, T.; Tsukada, N.; Yazawa, K.; Gyoung, Y. S.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1997, 62, 6274-6282.
32. (n) Rudolf, K.; Hawkins, J. M.; Loncharich, R. J.; Houk, K. N. J. Org. Chem. 1988, 53, 3879-3882.
33. (o) Hawkins, J. M.; Fu, G. C. J. Org. Chem. 1986, 51, 2820-2822.
34. (p) Liebeskind, L. S.; Welker, M. E. Tetrahedron Lett. 1985, 26, 3079-3082.
35. (q) De, A.; Basak, P.; Iqbal, J. Tetrahedron Lett. 1997, 38, 8383-8386.
36. (r) Yamamoto, Y.; Asao, N.; Uyehara, T. J. Am. Chem. Soc. 1992, 114, 5427-5429.
37. (s) Dumas, F.; Mezrhab, B.; d'Angelo, J.; Riche, C.; Chiaroni, A. J. Org. Chem. 1996, 61, 2293-2304.
38. (t) d'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112-8114.
39. (u) Mezrhab, B.; Dumas, F.; d'Angelo, J.; Riche, C. J. Org. Chem. 1994, 59, 500-503.
40. (v) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1849.
41. The stereochemistry of 3a was assigned by X-ray diffraction (X-ray data will be published in a full-paper), while the stereochemistry of the other major diastereomers 3b-j was assigned on the basis of their spectral and chemical-physical similarities with 3a. The stereochemistry of 6, derived from D-Ala-OMe 1a was determined by chemical correlation with 3a, after cleavage of the oxazolidinone auxiliary.
42. (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
43. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. See also:
44. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Org. Lett. 2000, 2, 747-750.
45. 3 in related reactions: Mero, C. L.; Porter, N. A. J. Org. Chem. 2000, 65, 775-781.
46. Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030. Oxazolidin-2-one auxiliaries were usually recovered in nearly quantitative yields after cleavage.
47. Only proline derived pseudo-tripeptide 7d, obtained as a ca. 3:1 mixture of isomers at the peptide bond, was isolated as a foam.
48. + + 1], 311 (93), 208 (30), 166 (30), 91 (100).